


An Unhealthy Obsession: Permanently Yours

by Sheiladine



Category: The Simpsons
Genre: F/F, F/M
Language: English
Status: In-Progress
Published: 2017-04-03
Updated: 2017-05-11
Packaged: 2018-10-14 14:56:39
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Underage
Chapters: 4
Words: 4,121
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10538790
Author URL: https://archiveofourown.org/users/Sheiladine/pseuds/Sheiladine
Summary: This is one of the three endings I created for the 'An Unhealthy Obsession' series... How would Lisa's life turn out if she returned to her normal timeline and still pursued Jimbo Jones?





	1. Party

Chapter 1

            Lisa Simpson never quite felt the same after her time travelling escapade when she was 15. She spent the next year being withdrawn and focused on her studies. Many would deem this behavior from her as normal, but she didn’t feel normal at all. She felt as if she no longer knew herself. There was the person that a part of wanted to be, Leah, and who she really was, Lisa. For the entire year Lisa wasn’t able to shake Jimbo from her mind, but she was always too afraid to confront him, let alone reveal her secret to him that she was Leah. She told herself that she was content with keeping her distance and not letting him know about who she actually was.

            16 year-old Lisa was keeping to herself in her bedroom as her 18 year-old brother Bart was throwing a house party downstairs while their parents were out. Lisa had protested that he shouldn’t be doing these types of things behind their parents’ backs, but ultimately she didn’t try to stop him since she really didn’t have any reason to.

            As Lisa was studying for an upcoming exam she realized she was extremely thirsty. She made sure that she was properly dressed in her thick red winter coat and dark red wavy skirt that went just above her knees before she went downstairs for a drink of water. She sifted her way through the drunken rowdy patrons; there was loud music and commotion happening all over the place. As Lisa was making her way through the living room Sherri and Terri yelled at her from the other side of the room to join them in a drunken-yet-childish game of spin-the-bottle.

“Lisa, don’t be a square, come over here and join us!” Sherri yelled.

“Yeah right, don’t even try to get her to come over here.” Bart commented.

            Lisa looked at the group with slight annoyance until she saw Jimbo in the back of the group, but it looked like instead of being an active participant he was attempting to watch over his visibly drunken sister. Lisa noticed Dolph part of the group as well and shuddered before hesitantly making the decision to walk over to them. She decided that the Jimbo being there was worth the risk.

            “Yuck, what if it lands on me?” Bart protested.

            “Jimbo’s here with his sister too ya numbnut, I doubt you’ll be that unlucky.” Terri commented.

            “Just do it once Lisa.” Sherri begged.

            Lisa continued to look at the group annoyed, but it was just a game of drunken kissing and plus she and some of the other patrons were only 16, so she knew they’d probably keep her from getting into any other trouble, so she entertained them by sitting down on her knees and taking a turn. Lisa glanced over at Jimbo, but he seemed preoccupied with getting his sister to try and behave. Lisa noted that his sister, Karen Jones, had turned out to be very attractive. She could understand the concern he had for her. She looked very intoxicated.  

“Fine.” Lisa said as she gave the bottle a spin.

            Lisa hoped it didn’t land on someone too awful, like her brother, Dolph, or… oh god, Milhouse was here as well? She mentally groaned at her stupid decision. It was fairly dark in the room, and she didn’t scope the people out as much as she should have.

            Lisa watched as the bottle was slowing and as she hoped to herself that it would land on Jimbo. She was mentally excited as it slowed near him, but was instantly disappointed as it slowly inched past him and landed onto his sister. Lisa didn’t quite compute how much trouble she got into until Karen started to giggle flirtatiously.  

“Come ‘ere you.” Karen mumbled with a drunken smile, Lisa looked back at her and gulped nervously.

            Karen embraced Lisa and kissed her suddenly and roughly, brushing her fingers through her hair. Both Bart and Jimbo stared at the two with a look that was between awestruck and disgust. It would’ve been attractive if it hadn’t involved their sisters, since Bart was visually attracted to Karen, and Jimbo didn’t mind Lisa too much, she was just too young for him to advance on her. Karen slipped her tongue into Lisa’s mouth and Lisa froze, letting Karen knock her over and get on top of her in order to continue to roughly kiss her. Other members of the group starting giggling drunkenly and the males of the group were eyeing them eagerly. Bart just groaned and gagged at the scene.

            Jimbo noticed the group’s and became a bit annoyed. He didn’t like people eyeing his sister like that, and he felt an inexplicable anger toward the people staring at Lisa in the same way. In a way he found himself a bit jealous of his sister. He went over and grabbed his sister off of Lisa.  

 “James! Quit gettin’ in my way of my fun-“ Karen snapped, hiccuped and fell backwards into him as he led her to an unoccupied chair to sit in.

            Lisa got up and mumbled,

“I’m done too….”

            Sherri and Terri jeered at her and called her a loser, but she ignored them. Lisa snuck off and headed toward Jimbo and Karen to check and see if Karen was alright, but secretly she just wanted to talk to Jimbo.

“Is she okay?” Lisa asked.

“Yeah… just drunk.” Jimbo replied.

            Karen mumbled something in a frustrated tone incoherently before passing out in the chair.

“Sorry about that…” Jimbo said in reference to the stunt his sister pulled earlier.

“Don’t be…” Lisa replied.

            The two looked away from each other awkwardly now that Karen was asleep.

            Lisa thought she would decide to be bold before he walked away from her. She knew it was a longshot because it would involve him leaving his sister in this chair by herself.

“You want to… go upstairs…?” Lisa mumbled, turning red.

            Jimbo looked at her incredulously, but he wanted to see if she was implying what he thought she was implying. He let his sex-drive dictate his thoughts instead of his brain and decided that Karen would be fine by herself for a while as he went upstairs to see what Lisa wanted…


	2. Another Mistake

Chapter 2

            Lisa shut her bedroom door once Jimbo stepped inside. She hurriedly wrapped her arms around him and kissed him. Lisa felt as if she just had a jolt of electricity go through her. She could feel all of her pent up emotions rising out of her as she continued to lock lips with him. Lisa’s actions shocked Jimbo, but he didn’t stop her. He decided there would be no harm in messing around with her a bit as long as he didn’t fuck her, since she wasn’t 18 yet he didn’t want to get nailed. She led him to her bed where they started to make out.

            Lisa took off her thick red jacket, but her tattoo was still covered by a maroon long sleeved shirt. She didn’t want to reveal her tattoo to him yet, if ever at all. Jimbo noticed how she started to grind up against him as she kissed him. He never imagined that he would ever be touching Lisa Simpson in any sort of sexual way since he never pegged her for the type. She was driving him crazy though and he felt like she was trying to ask for more than just some innocent kissing. He was trying to contemplate what he could do to her without actually sticking his dick in her. He didn’t want to leave any evidence that he was messing around with an underage, teenage girl, especially Lisa who seemed to be the epitome of innocent.

            Lisa knew that Jimbo was holding back, and she had an idea as to why. She wished there was a way to convince him that she wouldn’t get him in trouble if he had sex with her right here and now. She started contemplating ways to get him to cave in and give her what she wanted.

“I want you.” Lisa whined as she slid her hands up the back of his shirt and lightly scratched her fingernails down his back.  

“I know.” Jimbo smirked before getting on top of her.

            Lisa could feel his cock hardening through his pants. Jimbo slid his hands up her skirt and pulled her underwear off. She thought for a moment that he might actually fuck her, but she was surprised when he spread her legs, moved his face between her legs and started to lick around her clitoris. Lisa yelped in surprise before feeling tinges of pleasure. It wasn’t as good as him fucking her but she still felt rapid waves of pleasure from him tickling all of her sensitive spots with his tongue.

            Jimbo stopped momentarily and grimaced at the annoyance of his cock throbbing in his pants. Lisa felt bad and wanted to relieve him, but she couldn’t exactly make him fuck her. He got up and lied down next to her. He unzipped his pants and released his cock that stood up straight and throbbing. It caused Lisa to feel more electric jolts of want and need deep inside of her. She wanted him badly, but she knew that he wasn’t going to give himself to her that easily.

“Sit on my face so I can eat you out and jack off.” He said casually.

            Lisa’s face burned bright red, she didn’t know why, but him saying that out loud embarrassed her slightly. She was also upset that he wasn’t going to have full on sex with her.

“You know, we can just… do it.” She mumbled.

“You’re a bit young for that with me.” He was annoyed with her ignorance.

“It’s fine if it’s with you.” Lisa pleaded.

“I’d rather not take the chance.” Jimbo said hesitantly.

            Lisa sighed in defeat, and straddled his chest. Lisa paused momentarily and started contemplating to herself. She enjoyed his licking around, but she really wanted to feel his penis inside of her. She decided that she was going to take a chance, and that the worst that would happen is that he would just get annoyed at her like before then go back to oral play. Jimbo looked at her impatiently as she sat still. He thought she must’ve just been embarrassed since she was still blushing and seemed to be distracted by her thoughts, or being bitter about the rejection. He was about to say something to snap her out of it until she lifted herself up slightly. What happened next happened too quickly for him to protest.

            Lisa moved herself back and managed to guide his cock into her vagina. She slid herself all the way down, winced and whimpered loudly as her body trembled around his length. He was big and she hadn’t had sex in a about a year, also he was older and slightly larger than when she had been with him before, so it was a tight fit.

            Jimbo was momentarily stunned in shock by what she just did. He felt the walls of her vagina clench tightly around his cock and it felt maddeningly good, but he was also frustrated by her actions. He didn’t want to get royally fucked over by this, and on top of that there wasn’t a condom involved, so who knew what else could go wrong…

“Lisa get off! Fuck!” Jimbo snapped at her annoyed.

            He grabbed her by the hips and made an attempt to somehow push her off, but she resisted, grinding against him. Lisa was squeezing him so hard, and was so agonizingly tight that he wanted to burst. He resisted the urge to flip her over and fuck her brains out.

            Lisa tried to continue to slowly ride him, but he was so big that she could barely get herself to do it comfortably, but she didn’t want to get off of him. She liked the feeling of having him inside of her. Jimbo could tell she was hurting.

“Lisa-“

“N-no, I w-want this.” She whimpered.

            Jimbo knew that he would hurt her less if he was on top of her. He hesitantly made the decision to flip her over so that he was on top of her to relieve some of her pain. Lisa wrapped her arms around him to make sure if he tried to stop he would at least have to make a bit of an effort, she knew he was stronger than she was. Jimbo noted how she was trying her best to make sure he didn’t take himself out of her. He decided the damage was already done and started to thrust into her, but gently enough so she wouldn’t be in as much pain as she was when she was taking his entire length in while on top of him.

            Lisa was moaning in pleasure, and she knew the music and the commotion from the party outside were so loud that nobody would hear her. She noted his rhythms and started to grind back into him in an attempt to make him go deeper inside of her. Even if it hurt she wanted to feel all of him again.

“Lisa, let go. I have to…”

            But Lisa didn’t let go, and she made sure to hold on tighter. She wanted him to cum inside of her. She wanted all of him and she was so lost in her own lustful ecstasy that she didn’t care about any of the implications of the situation. Lisa herself knew that she wouldn’t ever get him in trouble for this, but nonetheless Jimbo was still concerned about the trouble he could get in. Not only did he stick his dick in trouble, but he would be leaving a lot of evidence in her too. He felt himself reaching the edge, and continued to beg her,

“Lisa, I mean it, I’m gonna cum-“

“I want you to… please...” She begged back as she thrusted her body back into his and continued to rub her nails down his back.

            He couldn’t hold it any longer. Without a condom and with her being so tight he just couldn’t keep himself from releasing. He felt himself empty into her, every last drop, and there was a lot of it, maybe more than usual, probably from the severe arousal and blue-balling he put himself through with her earlier. He whimpered a bit from the pleasure, and from the defeat of relieving himself inside of her. Lisa let out moans and whimpers of pleasure as well as she felt his hot, sticky cum fill her up and eventually start to drip out of her. She nuzzled into him as he lied on top of her, trying to comfort him like she used to. Jimbo noticed her actions and felt a wave of emotions come over him that he hadn’t felt in years. He felt embarrassed and ashamed of them since this was Lisa, and a girl who wasn’t even 18 yet.

            Jimbo quickly got back up once he regained his senses and zipped up his pants. He gathered himself and quickly left her room without saying a word to her. Lisa just sat there in slight emotional shock. She sat up and felt more of his semen spill out of her and onto her bed, but she didn’t care about the mess. She pulled her knees up to her face and began to cry. For another year he didn’t make any sort of verbal contact with her.


	3. Stalker

Chapter 3       

            Lisa was 17 when she had her next encounter with Jimbo. It had been nearly one year since her encounter with him at the party taking place inside of her home. This time Lisa took a more straightforward approach. Lisa actively sought out Jimbo when she left the house one day. Lisa didn’t decide on that day in particular to pursue him, but when she was taking a refreshing summer walk she happened to see him walking down the opposite side of the street that she had coincidentally happened to be walking on as well.

            When Lisa first saw Jimbo she hid herself. She didn’t want to scare him away, but she did want to follow him and confront him, just not where they were now. She hoped that he would go somewhere more secluded so she could confront him there. Eventually she did follow him to a spot where she was comfortable with confronting him. Lisa watched as he sat on a bench by the sidewalk he was walking on. Other than the road, the surrounding area was forested. Lisa sometimes walked down this road for some peace and quiet since it was fairly remote. She was happy he chose this spot, not just for the solidarity, but because she was becoming a bit tired from all the walking she had done for most of the day. Hiding was more exhausting than she thought it would be.

            Lisa noticed that he was lost in his own thoughts, so she would decide to try a more straightforward approach instead of sneaking up behind him. She quietly walked up to the bench he was sitting on and sat right next beside him. He didn’t notice her at first, but slowly turned his head to see who sat beside him and flinched back in shock.

“L-Lisa! What’re you doing here?”

“To see you… why else would I be here?” Lisa said innocently.

            Lisa moved closer to Jimbo, and leaned into him. She moved her hand to the top of his thigh. Jimbo looked at her nervously. It was another strange predicament that he didn’t like getting himself into.

“Lisa, I thought we already talked about this.”

“You mean a year ago? You just left…” Lisa said disappointedly before moving her hand up to his crotch. She moved her face close to his.

            Jimbo pulled himself away from her and hurriedly stood up off of the bench. Lisa looked up at him in frustration as he ran into the woods behind them. She hurriedly ran after him. Jimbo was surprised by how fast she was. He ran into a clearing and thought he had finally lost her when he felt her tackle him from behind. The two landed to the ground with a thud. Jimbo was honestly surprised by her actions. He didn’t think she would ever have it in her to pursue him and catch him off guard like that. Nevertheless he was feeling very unsettled by her. He was hoping to stay away from her after their last encounter. Lisa wrapped her arms around him and snuggled into him, refusing to let him go.

“You’re crazy, you know that?”

            Lisa ignored his comment and continued to snuggle into him.

“Fine, you win… this time.” Jimbo said defeated.

            Lisa giggled and moved so she was on top of him, laying her head against his chest.

“Get it over with. What do you want?” Jimbo asked annoyed.

“You.” Lisa replied in a flirty tone before giving him a kiss on the cheek.

“I really hope you don’t end up screwing me over for this-“

“I didn’t before, so why would I now?” Lisa said dreamily as she put one of her hands up his shirt and felt his bare skin.

            Lisa gradually moved her hand down to the button and zipper of his jeans, undoing both. Lisa slipped her hand under his boxer short and grasped his cock that started to instinctively harden from the reaction of her touch.

“You know, it’ll be hard to do it out here…”

“Oh, I wasn’t planning on doing that. I just wanted to focus on you.”

            Jimbo wasn’t sure what she was talking about until she lowered herself down so her face was near his cock. She licked the entirety of his length before inserting the head into her mouth. He shuddered and gasped. She started by only sucking on the head of his cock and teasing it with her tongue. He continued to gasp and whimper and she gradually went deeper. Lisa was trying her best not to cough or gag, and Jimbo couldn’t believe how amazing her mouth felt. He put his hand behind her head and stroked her hair as her mouth went up and down his length.

            Eventually Jimbo came and was pleasantly surprised when Lisa continued to lick and suck. She swallowed everything that he gave her. Jimbo panted and sighed in ecstasy. Lisa brought herself back up and placed her head back on his chest. His breathing relaxed her.

            After lying on the ground momentarily the two exchanged a few awkward words and parted ways.


	4. Lisa's Saxophone

Chapter 4

            When Lisa finally turned 18 she didn’t have any other reason not to pursue Jimbo Jones, but she didn’t exactly know how she should present herself to him. Even though she was now 18 what was really stopping him from running from her again? Thinking about that hurt her head and she decided what she really needed was some time to think to herself, preferably while playing her saxophone out in the fresh air.

            Lisa found a comfortable looking spot in one of the local parks. The park always relaxed her and filled her with pleasant memories. It felt like no time at all until Lisa lost herself in her thoughts and music. However, as tradition would seem to follow, Lisa was interrupted by three most known ruffians in Springfield, Jimbo, Dolph and Kearney. The three were also meandering around the park when Kearney and Dolph’s attentions were distracted by Lisa and her saxophone. Jimbo followed the two hesitantly, being careful not to display how much of a nervous wreck he was actually feeling in front of his friends.

“Well, look at this.” Dolph sneered before walking up to Lisa and snatching saxophone out of her hands causing her to scowl at him.

“This is pretty familiar, heh.” He tossed the saxophone over to Kearney and the two laughed.

“Can you _please_ not?” Lisa sighed as she watched Kearney laugh and throw the sax to Jimbo, who caught the instrument hesitantly, making an extremely forced yet nervous smile not trying to let his peers into his discomfort with the whole situation.

            Jimbo quickly threw the sax back to Dolph, but Lisa shot an angry glance at Jimbo momentarily before returning her attention back to Dolph.

“Stop joking around and give it back.” Lisa said annoyed.

“I don’t know. It could be worth somethin’. What do I get if I give it back?” Dolph smirked.

            Lisa stood up quickly, enraged.

“Are you kidding? It’s not yours to begin with. Give it here!” She snapped frustratingly, trying to get her instrument back, but Dolph deflected all of her attempts.

“Give it to me!” Lisa scowled angrily trying to grab her saxophone.

“I’ll give ya somethin’ alright, but it won’t be this piece of junk.” Dolph smirked again, and Kearney chuckled at his innuendo. “C’mon, give me something for this. If you want it bad enough you will.”

            Lisa looked over at Jimbo desperately, hoping that he would step in and do something to help her out of this situation. As he looked away nervously from her she knew he wouldn’t, so she turned back to Dolph.

“Quit lookin’ at your boyfriend over there like he’s gonna help you.” Dolph teased.

            Jimbo frowned and blushed red slightly and Lisa continued to scowl at Dolph over the comment. Ever since the incident at the party two years ago they had given Jimbo no mercy when it came to his escapade with Lisa since it wasn’t really the most discrete meeting ever. They were both easily able to figure out that what they were both doing alone in her room, and they never let him hear the end of it since then.

“Fine.” Lisa said bitterly.

“Haha, great.” Dolph said while setting the saxophone behind him. “What’re you going to-“

            Lisa interrupted Dolph by grabbing his shirt and forcing him into a kiss. She knew Jimbo was watching, so she went as to force her tongue inside of Dolph’s mouth and around of the inside of it as she pulled him closer to her. Eventually she knew that she made her point, and she decided to stop and let Dolph go before the shock wore off of him.

            Dolph stood there paralyzed for a moment while Lisa wiped her mouth with the sleeve of her jacket and picked up her sax. She walked away and looked at Jimbo as she was passing. She spat on the ground and left.

…       


End file.
